


As Sweet as Strawberry Wine

by WeAreTheLuckyOnes



Series: WATLO's Multi-Fandom Kinkfest [9]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Blow Jobs, Canon Divergence, Crossdressing, Cunnilingus, Established Relationship, Face-Fucking, Lingerie, Multi, Oral Sex, Pegging, Polyamory, Threesome - F/M/M, Threesomes
Language: English
Status: Completed
Published: 2020-05-16
Updated: 2020-05-16
Packaged: 2021-03-03 00:40:50
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,154
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24216070
Author URL: https://archiveofourown.org/users/WeAreTheLuckyOnes/pseuds/WeAreTheLuckyOnes
Summary: He'd heard Gabriel mention panties, and something about the way lace would look on him, and Sam remembered feeling a bit indignant at the thought of wearing women's underwear, then intrigued.
Relationships: Gabriel/Rowena MacLeod/Sam Winchester
Series: WATLO's Multi-Fandom Kinkfest [9]
Series URL: https://archiveofourown.org/series/1763266
Comments: 8
Kudos: 17





	As Sweet as Strawberry Wine

**Author's Note:**

  * For [nickelkeep](https://archiveofourown.org/users/nickelkeep/gifts).



> [Nickel](https://archiveofourown.org/users/nickelkeep), [Darmys](https://archiveofourown.org/users/Darmys) and I were talking about pegging and Sam in lingerie and my brain went places, so blame them for this. I also blame [Just Another Tart](https://justanothertart.tumblr.com) on Tumblr, because his pictures are the reason Nickel, Darmys and I even started the conversation about Sam in panties.
> 
> Title from Tennessee Whiskey by Chris Stapleton because Tennessee Whiskey by TrenchcoatBaby made me want to listen to it and apparently I now like country music? (‘Now’ is a lie, cause one of my favourite songs is Can’t Shake You by Gloriana and it has been for the last four years).
> 
> Panties are based on [these](https://www.honeybirdette.com/collections/briefs/products/molly-ivory-brief), which are currently at the top of my wishlist. 
> 
> Thanks to Nickel for the beta.

Sam's reminded of the talk he vaguely remembered Rowena and Gabriel having over the top of him the week before as he drifted in and out of consciousness after quite a few rounds of vigorous sex as he stares at the pair of lace panties he pulled from the inconspicuous black box he'd found on his bed. Rowena had been tracing lines between the moles on Sam's back, down his hips, and over the round of his ass, whispering to him about how lovely his skin was, how soft it was. Sam hadn't been paying much attention to her words, too spaced out and sore in the best ways, enjoying her gentle touch. He'd heard Gabriel mention panties, and something about the way lace would look on him, and Sam remembered feeling a bit indignant at the thought of wearing women's underwear, then intrigued. He never managed to insert himself into the conversation, too tired to speak, and he hadn't thought of it again afterwards, but he remembers it clearly now.

The underwear is a dark forest green, with little roses stitched into the front, and objectively, Sam decides they're really nice, and he'd be totally into Rowena in them. But he knows they're not for Rowena, and he hesitates to think of them for himself.

A note had been left on the box and Sam reads it now, Rowena's tiny flowy handwriting almost as indecipherable as ever; _Gabriel and I will be by later, I would love to see you in these_.

His gaze falls on the panties again, then the note, his heart racing in his chest and his cheeks warm with a strange mix of sheepishness and arousal. He knows Rowena's not demanding he wear them, she would never demand anything of him, and he thinks that's probably why he decides to do it. He approaches their sex life with a _try anything once_ attitude, and today won't be any different. 

He settles the letter back down on the bed and turns the panties over in his hand. _At least they're not a thong_ , he decides. He doesn't think he could come back from the mortification of seeing his brother in the kitchen the morning after wearing a _thong_. The back is plain cotton in the same forest green that settles down into a vee before morphing into the lace at the front, with a buckle at the top and a cut-out in the shape of a V. He's also glad there are no silly little bows anywhere in sight, 'cause he doesn't think he could take that

He hides the note and the panties in the box and puts the box in his closet in case Dean decides to go rifling through his bedroom while he's gone, then takes his towel and dressing robe to the showers. He turns the water on hot until his skin goes pink with it, before taking on the thorough clean he does of his body. He washes the sweat from his skin and the blood and aswang guts drying in his hair from him and Dean's hunt before moving onto a more thorough clean.

Once he's done he leaves his clothes in the hamper before stepping out into the hallway in a billow of steam wearing only the robe while he rubs the towel through his hair. He can hear Dean and Castiel in the other room, talking, the sounds of their footsteps before the heavy creak and thud as the bunker door is opened and then shut again. He's grateful the two are leaving, they both know about what Sam, Rowena and Gabriel get up to behind closed doors, but the thought of them home with what Rowena and Gabriel have planned for him is slightly horrifying.

He lets himself back into his bedroom and leaves the towel over the back of the desk chair before rifling through the top drawer for a hair tie to pull his hair back. He fusses about for a bit, putting his clean clothes away and his dirty things in the hamper, putting his toiletries back on top of the chest of drawers and leaving his now-empty duffle at the bottom of the closet before he realizes he can't put it off any longer. 

He takes the box out of the closet again and stares at it for a long time before pulling the lid open, taking out the panties, and replacing the box on the shelf. He strokes the material between his fingers, enjoys the soft feel of it, and wonders what it will feel like over his cock. The thought sends a shiver down his spine and a tingle in his groin, his cock chubbing up just a bit. He takes a final deep, settling breath before he unties his dressing gown and pulls it off of his body, hanging it over the hook next to the door. He holds the leg holes of the panties open and steps into them one by one, carefully sliding the material up his thighs, suddenly worried he might rip it. The material has a bit of a stretch to it, and it goes easily over his ass, settling onto his skin and fitting perfectly like it was made for him. He'd worried the front would be too tight and strangle his cock, but it's got just enough give that even with a hard-on it sits right where it's supposed to. Sam wonders if Rowena had it made specifically for him.

He smoothes his hand over the material, calloused fingers snagging on the lace before moving on. He's actually surprised how much he _doesn't_ hate it. 

He dresses over the top of the panties, jeans and an old Zepplin t-shirt he's pretty sure was Dean's first but has done the rounds so many times that he can't really be sure who owns it now. He doesn't bother with shoes and socks, padding barefoot out of the room and to the kitchen to have a beer before the archangel and the witch arrive. 

Gabriel appears first - literally - popping up in the kitchen as Sam’s finishing his beer with an easy smile and a gentle hand on Sam’s wrist as a greeting. He takes the pint of ice cream from the freezer and a spoon and climbs up onto the countertop to eat it, asking Sam about his hunt. (Sam knows Gabriel doesn’t really care for the answers to his questions, but he asks anyway because he knows _Sam_ cares.)

Rowena lets herself into the bunker through the front door not long after Gabriel has arrived, dropping her bag on the kitchen table and announcing, "I'll never work with other hunters again for as long as I live, you boys have spoiled me for manners and good hygiene practices."

Sam tries to decide when to slip it - that's he's wearing the panties Rowena bought him - into the conversation. He doesn't get the chance, though, because after Gabriel's done with the ice cream he climbs off of the counter, wraps an arm around Sam's waist, and shoves his hand into Sam's jeans. The move isn't particularly unusual for Gabriel (or Rowena), but it's still a bit of a shock.

Gabriel's face lights up when he feels the lace, like a kid in a candy shop (which Sam decides is an apt description for Gabriel). He turns to Rowena, and with a face full of wonder, says, "He's wearing them."

"Is he?" Rowena asks, practically skipping over to the both of them, reaching out and unbuttoning then unzipping Sam's jeans with no shame whatsoever, shoving his pants down to sit around his thighs. "Oh, yes, lovely. I have good taste."

Sam snorts at her and rolls his eyes, then says, "Unless you want to give Dean and Castiel a show they won't appreciate can we move this to my bedroom?"

They both back away and Sam buttons his jeans back up, not bothering to zip up, then starts towards the hallway and his bedroom. He waits at the foot of the bed for Gabriel and Rowena to join him (he thought they'd been following him - apparently not), a little self-conscious, but rather a lot less than he would be if he were only wearing the panties. When Rowena and Gabriel enter the room, they're whispering conspiratorially, and he knows it's about him. Considering it's a normal conversation for them, they're probably talking about how they want the night to play out, not bothering to include him in the conversation at all. He doesn't mind it, he thought he would at first, but he gets a kick out of it, and he knows if he truly wanted something or didn't want something and if he'd told them so, they would listen to him. 

Rowena lights the various candles around the room with the lighter Sam had left sitting on the bedside table (she has an aesthetic, Sam finds it weird but Gabriel doesn't, so Sam just sort of goes with it) while Gabriel takes Sam's face in his hands and kisses him. Gabriel kisses like a wildfire, fast and all-encompassing, with a wicked tongue and a gentle bite, a complete contradiction to the way Rowena kisses - deep and long and slow like honey. 

Rowena gets her fingers under the hem of Sam's t-shirt and begins to pull it up over his body, separating Gabriel and Sam's mouths for a moment as she pulls it over his head. She wraps her hands around Sam's shoulders and presses her mouth to his back in a gentle kiss. Sam really likes being pressed between the two - a powerful witch and an even more powerful archangel - he feels small and strangely taken care of, but he’d never admit it to the two because they’d spend the rest of his life smug and they’d never let him live it down.

Rowena slides her arm around Sam’s body, fitting it in between his and Gabriel’s chests to pinch and roll his nipple between her fingers. She replies to his moan with a delighted laugh and does the same to his other nipple before slipping her hand further down his body. She pulls open the button of his jeans and wiggles her hand inside, curving her palm around Sam’s cock and squeezing.

“Fucking hell.”

Gabriel laughs like he does every time Sam mentions God or hell while they’re having sex because he’s a fifteen-year-old boy trapped in the mind of a few tens of thousands year old archangel and the body of a Norse trickster god, and Sam reaches under his shirt to pinch _his_ nipple in retaliation. If anyone likes their nipples touched more than Sam or Rowena it’s Gabriel, and Sam uses that against him often.

Sam drops his hands to his sides and wiggles out of his pants, letting them pool at his feet and kicking them away, then says, “Right, I can’t be the only one naked so hurry up.”

Gabriel, the shit head, clicks his fingers and disappears his clothes while Rowena unties the wrap of her dress. Sam feels better then, less self-conscious, once he’s not the only one naked.

When he turns to look at Rowena he notices she’s wearing the same panties he is, but in white, with a bra that matches and he raises his eyebrows at her.

“What? I liked them, I wasn’t going to let you have all the fun.” She goes to Sam’s left side bedside table and starts rifling through the drawers before moving to the right side, humming in annoyance when she doesn’t find what she’s looking for. “Where’s the…”

Sam doesn’t bother asking what she means and instead climbs to his knees on the floor next to the bed and pulls out the box he holds Rowena’s strap-on in. “I put it under here when you’re not over, Dean likes to go through my drawers.”

“That’s a very nice look on you,” Gabriel says with a cheeky grin. “You on your knees.”

Sam climbs to his feet and rolls his eyes good-naturedly then says, “If you’re angling for me to kneel on the stone floor and suck you off it’s a hard no. _Stone floor_.” He pats Gabriel’s cheek and sits on the bed with the box, opening it up and throwing the item inside at Rowena. 

She catches it and wiggles it at Sam. He’s in love with two adult children. “Did you clean it?”

“Obviously, what do you take me for?”

Rowena rolls her eyes at him before tucking a thumb under the waistband of the panties she’s wearing, humming thoughtfully. “On or off?”

Gabriel pipes up then, approaching Sam and reaching up to pull out the tie in Sam’s hair, running his fingers through the strands. Sam won’t admit it, but Gabriel’s one of the main reasons he won’t cut his hair, he enjoys the feeling of Gabriel scratching at his scalp and pulling at his hair too much. “On. You match.”

Sam drops his eyes from Gabriel’s down to his crotch where his cock juts out from his groin, hard and flushed red. He reaches out for it, grasping him around the base and leaning forward to take the head into his mouth. The angle is awkward, he’s too tall and he has to crane his neck to reach, but he can’t find it in himself to care when he’s making Gabriel whine like that. He licks at the tip and, prodding at the precome dribbling from the slit with the tip of his tongue. He swallows further around the length of Gabriel’s cock, taking as much as he can without gagging, before pulling off.

Sam rubs out the ache in his neck and says, “Can you lay down? If I do it like that any longer my neck might break.”

Gabriel sits up against the headboard and Sam settles in between his knees on his belly. Before he can get his mouth back on Gabriel, Rowena grumbles and he turns to look at her. She’s got the fake cock strapped on, but the angle isn’t right and it’s too low down; Sam has no idea how she does it wrong every time.

“Bloody thing,” she swears, dropping her hands to the side in defeat and stepping up to the bed so Sam can fix it for her like he always does.

“You’re a powerful four-hundred-year-old witch and a strap on is what stumps you?” Gabriel teases, watching as Sam sorts Rowena out. Rowena gives him the finger in retaliation.

Once Sam’s done he goes back to Gabriel’s cock, sucking it into his mouth and hollowing his cheeks as he slides down. Gabriel lets out a low groan that’s muffled when Rowena leans over to kiss him, tongue licking out and into his mouth. Sam gets distracted by the sight, and can’t manage to do more than lay there with Gabriel’s cock settled onto his tongue, which Gabriel doesn’t like at all. He gets his hand in Sam’s hair and thrust his hips up, fucking his cock into Sam’s mouth without even pulling his own away from Rowena’s. 

The first few thrusts make Sam gag until he has enough mind to relax his throat, then he digs his fingers into Gabriel’s thighs and holds on as the archangel fucks his mouth. He'd closed his eyes, so he hadn't known Rowena had pulled away from Gabriel until he feels her small, warm hand on the skin at the base of his spine, her finger pulling the panties off to the side. A cold, slick finger strokes over the furl of his asshole and Sam groans around Gabriel's cock at the shiver it sends up his spine. His own cock suddenly throbs, and Sam's suddenly reminded of it, reminded it hasn't been touched since Rowena slid her hand into his pants, reminded it's still trapped in the lace of the panties. He reaches his hand down and grasps the shape of his cock to relieve the pressure. 

"Wait, pet," Rowena says gently, extracting his hand, settling it back on Gabriel's thigh. "You know you hate being fucked right after you've come, and I'm not going to wait just because you couldn't."

Sam rolls his eyes behind his eyelids, despite knowing Rowena won't be able to see it, but acquiesces, gripping Gabriel's hip to stop himself from reaching down again. Rowena fits the first finger inside of him and it goes in easily, with very little give. Her fingers are short, and they only just reach his prostate, but she makes up for that by gently scratching at it with her nail. When the three of them first started sleeping together Sam wouldn't let her finger him 'cause he was too terrified of her claws, so he always did it himself, or Gabriel would, but when he finally did let her she was gentle, not so much as a scratch, let alone the gouge he was expecting.

Rowena strokes his prostate for a few moments, long enough that Sam loses track of time, before pulling her finger out and replacing it with two. Sam breathes harshly in through his nose and pulls off of Gabriel's cock before he chokes on it. Gabriel's hand in his hair has turned from ruthless tugs to gentle stroking and Sam leans into and presses his face to the archangel's thigh as Rowena fingers him open. 

When she decides he's ready she pulls three fingers from him and pats his hip. He hears her rifle around in the sheets, then the snick of the cap on the lube opening before the cold head of the fake cock is pressing against his body. He braces himself against Gabriel's body and pushes back onto the cock spearing him open, bearing down on it until it slides fully into his body and his ass is pressed to Rowena's hips. Her first few thrusts are gentle, they always are, until she builds up momentum, finally starting to fuck into him how he likes it - fast and hard enough to make him breathless. She's holding the panties to the side with her thumb tucked under the material and her hand spread wide over his flesh. 

For a while, Sam can't do much more than lie there and take it, but he eventually realizes Gabriel's been waiting for him to get his shit together for ages and he's starting to get impatient - if the hand tugging at his hair is anything to go by. He gets his mouth back on Gabriel's cock and sucks it in deep, hollowing his mouth and dragging his tongue along the underside.

"Fuck, Sam," Gabriel groans, spreading his fingers out over the back of Sam's head and grinding his cock into Sam's mouth, rolling his hips. "God, you look so gorgeous, stuffed full of cock. I'm so glad you wore the panties, you look so lovely in them." Sam's not all that partial to dirty talk, but Gabriel loves it, loves doing it. He loves talking when they're not having sex, Sam still has no idea how he was surprised when Gabriel didn't shut up the first time they fucked. "That's it, sweetheart, you take my cock so well."

Sam pulls his mouth from Gabriel's cock and digs his tongue into the slit, lapping at the precome until Gabriel's groaning. Sam knows when he's about to come because his words morph from English to Enochian, jumbled words Sam can barely decipher. Sam swallows his cock again and hollows his cheeks, reaching up to roll and squeeze Gabriel's balls in his hand. He keeps sucking and kneading until he feels Gabriel's body go rigid, come spilling into his mouth. He doesn't manage to swallow it all, and it dribbles out of the corner of his mouth from around Gabriel's cock, spilling onto Gabriel's thighs. When Sam pulls off of him he swallows what's left in his mouth and breathes in deeply, trying to get oxygen back into his lungs.

He lays his face on Gabriel's thigh and reaches down to take his cock out of the panties, grasping it in his hand and squeezing. "Harder, fuck me harder," he tells Rowena over his shoulder, thrusting his hips back on Rowena's fake cock, meeting her thrusts in a slap of skin. Rowena fucks him harder, grip tightening over his waist and Sam is _so fucking close_. Gabriel's fingers are still in his hair and they've gone gentle again, scratching at his scalp in a way that makes Sam's body hum pleasantly. It's soothing, and Sam could almost fall asleep (if it weren't for the dick in his ass). 

When Sam comes, he groans a jumbled blend of their names into Gabriel's name and his body shudders, come spilling onto the sheets under him. Rowena carefully pulls the fake cock from his hole and he collapses, rolling onto his back with his head between Gabriel's thighs, chest heaving. 

"Give me a second," he tells Rowena, holding up his finger as he tries to catch his breath. Rowena's got a very smug look on her face and Sam rolls his eyes before patting his chest and saying, "C'mon, then." Rowena's smile gets even smugger, and she takes off the strap-on throwing it onto the floor to deal with later. She does it every time, despite how much he hates it, 'cause it means he'll have to clean it and then sterilize it and it takes _forever_ (because he's not letting her put it in him unless it's fully clean). She goes to pull the panties off and he stops her, "Wait, leave them on."

Rowena grins and climbs on top of him, shuffling her way up his body with Gabriel's help until she sits over him, her groin above his mouth. Her knees settle into the mattress on either side of Sam’s head in between Gabriel’s thighs, her hands reaching down to move Sam’s hair out of the way so she doesn’t pull at it. He hears the slick noises of Gabriel and Rowena kissing and looks up to watch them for a moment before he reaches up and slides Rowena’s panties to the side, settling the crotch in the crook of her thigh.

He blows a breath of hot air over where she’s dripping slick and flushed red already, so turned on just from fucking Sam with her fake cock. He spreads her folds open with his thumbs and flattens his tongue as he licks a thick stripe from her hole to her clit. She shudders and moans, reaching down to curl her fingers in his hair as he licks over her pussy in broad strokes. 

Rowena, unlike Gabriel, is pretty easy to get off. Well, maybe not easier, but certainly quicker. Fucking Sam (and occasionally Gabriel) with the strap on always makes her wet and desperate, and Sam barely needs to mouth at her clit and stretch her open with his fingers before she's coming, body spasming around his fingers.

On one upstroke of his tongue, he circles her clit, then comes back down to spear his tongue into her hole and she shivers, grinding down onto his face. He slides his hands up her ass to hold her at her waist, keeping her hips still as he fucks his tongue up into her. Her slick drips down his chin and he feels his cock twitch in renewed interest.

Gabriel is talking to her and Sam knows he’s urging her on despite being unable to hear him through the blood rushing in his ears. Sam licks up to her clit again and wiggles his hand underneath her, fitting the top of his index finger against her folds, stroking through her slick. He slides his finger inside her and crooks it towards her clit, searching for her g spot. She groans, her hips jerking up when he finds it and rubs it with the tip of his finger. She comes with a shout, her body shaking as he's sucking her clit into his mouth, scraping the teeth over the sensitive flesh. Sam licks her through the aftershocks, gentle now, until she lifts up onto her knees, away from his mouth, collapsing against the headboard next to Gabriel, chest rising and falling rapidly as she catches her breath.

"Can I take these off now?" Sam asks, snapping the waistband of the panties where it sits, still tucked under his balls. A fresh bout of self-consciousness is hitting him, and while in the act, knowing he was wearing women's underwear for Gabriel and Rowena was definitely very hot, but now it makes his skin itch.

Rowena reaches down and cups Sam's face smiling kindly. "Go on, love, and get a flannel while you're at it, all these various bodily fluids are gonna start getting real uncomfortable real soon."

Sam rolls over and climbs to his knees, leaving them both with a kiss to find a rag.


End file.
